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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: jezzielee on June 19, 2014, 03:25:53 PM

Title: Stuck on Claisen(?) reaction
Post by: jezzielee on June 19, 2014, 03:25:53 PM
I have been trying to figure out this problem since last night but I have no clue where to even start, I think it is a claisen reaction problem though. Thanks!
Title: Re: Stuck on Claisen(?) reaction
Post by: discodermolide on June 19, 2014, 03:37:45 PM
What do you know about the reactivity of the CH2 group of dimethyl malonate with a base and then an electrophile?
Title: Re: Stuck on Claisen(?) reaction
Post by: jezzielee on June 19, 2014, 03:45:37 PM
Quote from: discodermolide on June 19, 2014, 03:37:45 PM
What do you know about the reactivity of the CH2 group of dimethyl malonate with a base and then an electrophile?

Well I think a carbanion forms and it is alkylated with an electrophile
Title: Re: Stuck on Claisen(?) reaction
Post by: discodermolide on June 19, 2014, 03:51:49 PM
Ok do that then and see what you get when one of the bromines is displaced.
Title: Re: Stuck on Claisen(?) reaction
Post by: jezzielee on June 19, 2014, 04:04:36 PM
Quote from: discodermolide on June 19, 2014, 03:51:49 PM
Ok do that then and see what you get when one of the bromines is displaced.

So far this is what I was able to figure out
Title: Re: Stuck on Claisen(?) reaction
Post by: discodermolide on June 19, 2014, 04:06:49 PM
The first alkylation gives the diester you drew:
BrCCCCC([H])(C(OC)=O)C(OC)=O
The next reagent is NaOMe, so another alkylation:
you forgot the Br